I've been organizing the Low-Key Hillclimbs, with one extended break, since 1995, and as a cycling event it has always has always had its existence firmly planted in the internet. It was relatively early in that regard.
One feature of every year is a banner image. Banner images are rather dated these days, but I still like them. Here's a brief history of the Low-Key Hillclimbs banner image. One note: the 1995-1998 pages were reconstructed, since they had been inadvertently lost. 1995-1997 were regenerated with original graphics, but 1998 was generated fresh in 2008 from 1998 result data. So the 1998 banner image is circa ten years later.
1995: Rendered with a crude X11 paint program, using silouette of Marco Pantani
1996: Bolder font, tightened, but otherwise similar
1997: Intensity was the theme (slight irony), against green background
1998: Original web pages no longer available; this was basically a copy of 2008
2006: The Comic Sans was supposed to represent Low-Key. I alpha-channeled year.
2007: I scripted the year, and changed the text color
2008: Copy of 2007
2009: Another copy of 2007
2010: I graded the text color and reduced opacity on year
2011: New design, using a metallic text tutorial for Gimp
2012: Copy from 2011; I actually coped and pasted 2nd 2
2013: No "3" to copy, so new design: colors more plastic, with nova in background, using Gimp
2014: Fun with Gimp render filters, Mt Hamilton paceline in background, and improved year placement
I am a big fan of compact file size, as I can't expect everyone to have maximum bandwidth 24/7. But of course file size budgets have increased over the years. 1995 was 4-bit GIF mapped to the Netscape Color Cube. By 2014, it's 24-bit color with 8-bit alpha channel. Still, compared to the vast majority of the web, the Low-Key pages are exceptionally compact. This policy paid off with the explosion of mobile device web access. I have no need for mobile versions of the Low-Key pages: they were already mobile-compatible.
The 2014 design I did yesterday afternoon on my train commute, and finished it off this morning sipping tea (decaf black, mixed with a protein-fiber-vitamin drink mix and a bit of Stevia... yum, yum). Every year I go into it thinking perhaps that year is the last year for Low-Key. Every year needs to have freshness, needs the support of my co-conspirators, and needs to address the key concerns of all involved in things which can be improved. Every year needs to be better than the one before.